Sodium hydride → 7-Fluoro-2-methyl-2,4,5,10-tetrahydropyrazolo[3,4-b][1,5]benzodiazepin-4-one

HRID 1153854Notes

Reaction equation

CS([CH2-])=O.[Na+].[H-].[Na+].[NH2:8][C:9]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:10]=1[NH:11][C:12]1[C:16]([C:17](OCC)=[O:18])=[CH:15][N:14]([CH3:22])[N:13]=1>CS(C)=O>[F:27][C:25]1[CH:24]=[CH:23][C:10]2[NH:11][C:12]3=[N:13][N:14]([CH3:22])[CH:15]=[C:16]3[C:17](=[O:18])[NH:8][C:9]=2[CH:26]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of sodium methyl sulphinyl methanide was generated by stirring sodium hydride (50% oil dispersion, 1.5 g) in dry dimethylsulphoxide (15 ml) at 65° C. until gas evolution ceased. A solution of ethyl 3-(2-amino-4-fluoroanilino)-1-methylpyrazole-4-carboxylate (2.7 g) dissolved in dry dimethyl sulphoxide (5 ml) was added dropwise and the mixture stirred at 65° C. for 20 minutes. The mixture was poured on to excess ice-water, filtered and dried to give the title compound which was crystallised from chloroform-hexane m.p. 264° C.

Workup

additionwas added dropwise
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-299f347667914d7cb98c16500adfcc49
Source dataset: uspto-grants-1984_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04486591

Reaction notes

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